Isorhamnetin 3-[3'''-feruloylrhamnosyl(1→6)galactoside - Compound Card

Isorhamnetin 3-[3'''-feruloylrhamnosyl(1→6)galactoside

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Isorhamnetin 3-[3'''-feruloylrhamnosyl(1→6)galactoside

Structure
Zoomed Structure
  • Family: Plantae - Caryophyllaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Derivative
Canonical Smiles COc1cc(/C=C/C(=O)O[C@@H]2C(O)[C@H](OCC3O[C@@H](Oc4c(oc5c(c4=O)c(O)cc(c5)O)c4ccc(c(c4)OC)O)C(C([C@H]3O)O)O)OC([C@@H]2O)C)ccc1O
InChI InChI=1S/C38H40O19/c1-15-28(44)35(56-26(43)9-5-16-4-7-19(40)22(10-16)50-2)33(49)37(53-15)52-14-25-29(45)31(47)32(48)38(55-25)57-36-30(46)27-21(42)12-18(39)13-24(27)54-34(36)17-6-8-20(41)23(11-17)51-3/h4-13,15,25,28-29,31-33,35,37-42,44-45,47-49H,14H2,1-3H3/b9-5+/t15?,25?,28-,29-,31?,32?,33?,35-,37+,38-/m0/s1
InChIKey AFJSSOKKLPPJLD-JFJDFXGTSA-N
Formula C38H40O19
HBA 19
HBD 9
MW 800.72
Rotatable Bonds 11
TPSA 293.96
LogP 0.59
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 57
Formal Charge 0
Fraction CSP3 0.37
Exact Mass 800.22
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Herniaria fontanesii Caryophyllaceae Plantae 115623

Showing of synonyms

  • Mbark AN, Guillaume D, et al. (1996). An acylated isorhamnetin glycoside from Herniaria fontanesii. Phytochemistry,1996,41(3),989-990. [View]
Pubchem: 44259354
Nmrshiftdb2: 70093999

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 800.72 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OCC3CCCC(O3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 800.72 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 800.72 g/mol

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 800.72 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OCC3CCCCO3

Level: 2

Mol. Weight: 800.72 g/mol

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 800.72 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 800.72 g/mol

Structure

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 800.72 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 800.72 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 800.72 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 800.72 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 800.72 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 800.72 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.58
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
48.600
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
7141.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.880
Plasma Protein Binding
44.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-166.680
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.100
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-12959786.720
Rat (Acute)
2.320
Rat (Chronic Oral)
4.450
Fathead Minnow
16367.000
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
1450369.970
Hydration Free Energy
-2.920
Log(D) at pH=7.4
1.250
Log(P)
1.54
Log S
-6.24
Log(Vapor Pressure)
-47736.61
Melting Point
221.64
pKa Acid
-309.16
pKa Basic
3.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9713
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9713
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9518
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9518
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9339
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9339
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9163
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9163
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9018
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9018
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8925
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8925
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8810
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8810
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8797
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8797
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8773
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8773
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8707
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8707
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8489
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8489
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8482
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8482
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8371
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8371
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8358
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8358
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8269
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8269
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8231
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8231
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8083
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8083
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8066
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8066
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8057
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8057
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8000
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8000
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7907
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7907
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7822
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7822
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7801
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7801
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7770
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7770
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7769
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7769
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7760
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7760
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7744
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7744
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7741
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7741
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7722
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7722
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7683
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7683
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7664
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7664
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7650
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7650
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7645
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7645
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7637
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7637
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7628
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7628
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7615
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7615
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7598
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7598
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7585
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7585
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7584
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7584
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7578
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7578
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7553
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7553
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7515
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7515
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7482
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7482
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7444
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7444
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7435
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7435
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7426
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7426
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7400
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7400
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7395
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7395
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7363
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7363
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7332
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7332
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7330
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7330
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7315
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7315
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7309
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7309
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7288
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7288
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7241
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7241
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7223
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7223
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7221
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7221
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7215
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7215
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7176
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7176
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7161
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7161
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7139
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7139
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7112
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7112
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7112
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7112
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7097
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7097
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7091
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7091
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7089
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7089
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7082
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7082
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 4 0.7078
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 4 0.7078
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7067
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7067
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7046
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7046
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7034
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7034
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7018
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7018
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7017
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7017
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7013
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7013

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